cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt
• 英文别名: 3-O-β-D-glucopyranosylcyanidin trifluoroacetic acid salt；cyanidin 3-O-β-D-glucopyranoside trifluoroacetate；cyanidin 3-β-D-glucopyranoside trifluoroacetate；cyanidin 3-glc trifluoroacetate；cyanidin-3-O-glucoside trifluoroacetate；(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;2,2,2-trifluoroacetate
• 化学式: C₂F₃O₂*C₂₁H₂₁O₁₁
• 分子量: 562.407
• InChiKey: DETXGQYHIBRDLM-UBNZBFALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  221
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 cyanidin-3-O-glucoside hydrochloride
  参考文献：
  名称：

  EP1683805

  摘要：

  公开号：
• 作为产物：
  描述：

  (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 在 palladium dihydroxide 咪唑 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 甲基磺酰氯 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， -40.0~80.0 ℃ 、101.33 kPa 条件下， 反应 25.5h， 生成 cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt
  参考文献：
  名称：

  Novel and Efficient Synthesis of Cyanidin 3-O-β-d-Glucoside from (+)-Catechin via a Flav-3-en-3-ol as a Key Intermediate

  摘要：

  A novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route. From (+)-catechin, 3-OH was glucosylated, and the 4-position of the nucleus was then oxidized and dehydrated to give the 5,7,3', 4'-tetra-O-(tertbutyldimethylsilyl) flav-3-en-3-ol-3-O-glucoside (8) as a key intermediate. 8 was deprotected and oxidized under air in hydrogen chloride-MeOH to give 1.

  DOI：

  10.1021/ol0614976

文献信息

• The First Synthesis of 3-O-Methylcyanidin and the Effect of 3-O-Substitution on Stability Under Acidic Conditions
  作者：Kumi Yoshida、Asmaa B. El-Meligy、Takehiro Ishihara、Kin-ichi Oyama、Ahmed M. El-Nahas

  DOI：10.3987/com-18-s(t)74

  日期：——

  The simplest and most common anthocyanin in nature is 3-O-glucosylcyanidin (1), and 3-O-glucosylation is believed to stabilize the chromophore. To clarify the effect of the glucose residue we compared the stability of 1 with its aglycone, cyanidin (2), and newly synthesized 3-O-methylcyanidin (3). In an aqueous solution at pH 1, 1 and 3 showed similar stabilities, and 2 was less stable than 1 and 3, indicating that 3-O-substituion does enhance stability. We also analyzed the co-pigmentation effect of flavocommelin (4) and rutin (5), on the color and stability of 3-O-substituted cyanidins and cyanidin. The bathochromic shift of lambda vismax and stability of the color by addition of 4 was greater than that of rutin (5). 4 might stack closer and stronger to the anthocyanidin chromophore than 5.